Booking Flights with Miles and Points

OK, so you’re dying to travel the world for free and want to know who to get started–you’ve come to the right place. We’ll have a series of “getting started” guides to coach you along the way.

1. Pick your destination

Start by trying to narrow down where in the world (literally) you want to go. This might not be a difficult part for you but it helps to be flexible–to an extent–if you’re trying to book with miles. Use the following charts and info to get an idea of how many miles it’ll take to get where:

Airline Award Charts
Interactive Delta Award Maps
United MileagePlus Awards Map – Economy

2. Research how to get there

Once you’ve narrowed down your choice to a region or country (don’t forget that the more flexible you are the more luck you’ll have booking), you’ll need to start scouring your airline’s website for award ticket availability. If your points are on United, you’re in luck. These are wildly flexible, you’ll have an excellent experience in finding award availability and in maximizing your points–we go out of our way to rack up United points and have successfully booked two of our bigger trips using them. Delta, on the other hand, will waste your time, energy and effort while leaving eroding all of your hope for future travel. But it is possible.

3. Rack up miles

This step really goes with/before step 2. After researching when/where and how (through airline’s websites) you’ll want to find out how to get those precious miles necessary to get your ass off the couch and go off jet-setting. These two steps really go hand in hand, for example, if there’s a 50k mile signup bonus for United AND British Airways and you want to go from Atlanta to Paris, you’ll need to check both airlines first to see which has the lowest fees, availability for your preferred dates etc. It becomes a bit of a chicken-egg dilemma. Good credit cards to research:

(As of July 3)
50k Amex Points –> Business Gold Rewards Card from American Express
50k Chase Ultimate Rewards Points –> Chase Ink Plus (business card)
40k Chase Ultimate Rewards Points –> Chase Sapphire Preferred (personal card)

4. Start the booking process


TIP: When booking with miles you have to be flexible with either destination or time.  You can absolutely book a 25k Delta Skymiles domestic round-trip award with limitless flexibility on time, now you may have to go to a shithole like anywhere in Ohio or the Midwest but you can certainly go somewhere. So, just keep in mind that if you’re inflexible on dates you’ll need to be flexible on destination, and vice-versa.